Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto

A compound of Formula (I)

• or a pharmaceutically acceptable salt, solvate, and/or prodrug thereof,
• wherein:
• X is selected from S, S(O), and SO2;
• R1 is selected from H, C1-C6alkyl, C1-C6alkyleneP(O)(OR11)2, C1-C6alkyleneOP(O)(OR11)2, C(O)R11, CO2R11, C(O)N(R11)2, S(O)R11, and SO2R11;
• R2 is selected from H, halo, and C1-C6alkyl;
• R3 is selected from H, CN, halo, C1-C6alkyl, C2-C6alkenyl, and C2-C6alkynyl;
• R4 is selected from H, CN, halo, C1-C6alkyl, C2-C6alkenyl, and C2-C6alkynyl;
• R5 is selected from H, CN, halo, C1-C6alkyl, C2-C6alkenyl, and C2-C6alkynyl;
• R6 is selected from H, C1-C10alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkyleneZR12, C2-C6alkenyleneZR12, C2-C6alkynyleneZR12, C3-C7cycloalkyl, C3-C10heterocycloalkyl, C6-C10aryl, C5-C10heteroaryl, C1-C6alkyleneC3-C7cycloalkyl, C1-C6alkyleneC3-C10heterocycloalkyl, C1-C6alkyleneC6-C10aryl, and C1-C6alkyleneC5-C10heteroaryl, the latter eight groups being optionally substituted with one to four substituents independently selected from halo, C1-C6alkyl, OR13, and C(O)R13;
• R7 is selected from H, halo, and C1-C6alkyl;
• R8 is selected from H, halo, and C1-C6alkyl;
• each R9 is independently selected from halo, C1-C6alkyl, OH, OC1-C6alkyl, C1-C6alkyleneOH, and C1-C6alkyleneOC1-C6alkyl;
• R10 is selected from H, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkyleneZ′R14, C2-C6alkenyleneZ′R14, C2-C6alkynyleneZ′R14, C3-C7cycloalkyl, C3-C10heterocycloalkyl, C6-C10aryl, C5-C10heteroaryl, C1-C6alkyleneC3-C7cycloalkyl, C1-C6alkyleneC3-C10heterocycloalkyl, C1-C6alkyleneC6-C10aryl, and C1-C6alkyleneC5-C10heteroaryl, the latter eight groups being optionally substituted with one to four substituents independently selected from halo, C1-C6alkyl, OR15, and C(O)R15;
• Z is selected from O, C(O), NR16C(O), NR16C(O)O, C(O)NR16, OC(O)NR16, and NR16;
• Z′ is selected from O, C(O), NR17C(O), NR17C(O)O, C(O)NR17, OC(O)NR17, and NR17;
• n is an integer selected from 0, 1, 2, 3, and 4;
• R11 is independently selected from H and C1-C6alkyl;
• R12 is selected from H, C1-C6alkyl, C3-C7cycloalkyl, C3-C10heterocycloalkyl, C6-C10aryl, and C5-C10heteroaryl, the latter four groups being optionally substituted with one to four substituents independently selected from halo, C1-C4alkyl, OC1-C4alkyl, and C(O) C1-C4alkyl;
• R13 is selected from H and C1-C6alkyl;
• R14 is selected from H, C1-C6alkyl, C3-C7cycloalkyl, C3-C10heterocycloalkyl, C6-C10aryl, and C5-C10heteroaryl, the latter four groups being optionally substituted with one to four substituents independently selected from halo, C1-C4alkyl, OC1-C4alkyl, and C(O) C1-C4alkyl;
• R15 is selected from H and C1-C6alkyl;
• R16 is selected from H and C1-C6alkyl;
• R17 is selected from H and C1-C6alkyl, and
• available hydrogen atoms are optionally replaced with a halogen atom and/or available hydrogen atoms are optionally replaced with deuterium.